


Cupid's Error (You Mocha Me Crazy)

by writeonclara



Series: Cupid's Arrow [1]
Category: Supernatural
Genre: Alternate Universe - Soulmates, Coffee Shop Owner Gabriel, Feels, Fluff and Angst, Hijinks & Shenanigans, Lawyer Sam Winchester, M/M, Mechanic Dean, Oblivious Sam Winchester, Pranks and Practical Jokes, Puns & Bad Pickup Lines, Romantic Comedy, Teacher Castiel
Language: English
Status: Completed
Published: 2016-02-01
Updated: 2018-03-09
Packaged: 2018-05-17 13:18:41
Rating: General Audiences
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 6
Words: 13,735
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/5871124
Author URL: https://archiveofourown.org/users/writeonclara/pseuds/writeonclara
Summary: <blockquote class="userstuff">
              <p>Gabriel has a good life. His coffee shop, Paradise Found, is successful. He's got at least one sibling he gets along with. He's been thinking about getting a dog. The point is, Gabriel's <i>happy</i>.</p>
<p>And then Sam Winchester strolls into coffee shop and it's like getting shot in the chest. Gabriel is <i>gone</i>. It's too bad he doesn't seem to ping on Sam's radar like, at all, but Gabriel's got this. He's the socially capable one in the family, after all.</p>
<p>(The cupid <i>meant</i> to mark them both. It's just too bad he had to leave the job half-finished, but what could go wrong? Sam and Gabriel are soulmates, after all.)</p>
            </blockquote>





	1. Prologue

There was a cupid sitting in a mostly empty coffee shop. He was big, and naked, and he was watching the bored owner with his head tilted curiously to the side. He'd been watching him for the past twenty minutes. The cupid knew everything about the owner, having been briefed on him upstairs before he started his rounds.

 **Name:** Gabriel Milton  
**Age:** 35  
**Profession:** Owner of the popular coffee shop, Paradise Found  
**Soulmate** —

The door to the coffee shop swung open, little bells tinkling to announce the new customer. The man was huge, floppy brown hair swept back and black framed glasses perched on a straight nose. He held out a blue credit card to Gabriel and said, “Coffee, medium.”

Gabriel barely glanced up at the large man, ringing him up with bored efficiency. “Room for milk?”

“Please.”

It was as if they didn't even realize the _significance_ of this moment, the meeting of two souls that were literally made for each other. Samuel Winchester barely even glanced at Gabriel Milton when the cup of coffee exchanged hands. Gabriel didn't even blink when their fingers brushed.

Well. If the course of love always ran smooth, the cupid would be out of a job. He lifted a hand towards Gabriel and crooked his fingers. Gabriel jerked forward as if he had tripped, though he'd been standing still. He clutched the edge of the counter, eyes wide and startled.

The cupid beamed to himself. He just adored that look of the newly in love.

He turned to Samuel. The other man clearly wasn't aware of the blessing he was about to receive—

Abruptly, the cupid froze. He cocked his head to the side. “I'm in the middle of a job.”

He listened, face crumpling. Gabriel was staring Sam, stunned.

“Well, alright,” the cupid said. It was unusual to leave a job half finished like this. But Gabriel and Sam were meant to be! Even if Sam hadn't been marked, surely they would eventually find their way to each other.

What could go wrong? They were soulmates, after all.


	2. Meant to Bean

Paradise Found was always slow this time of day. Gabriel was beginning to regret enforcing the 'no cellphones at the register' rule. In the past hour, only one customer had popped in and Gabriel was slowly going crazy with boredom. 

The bell over the door tinkled and a huge man strolled in, brown hair perfectly swept back and black framed glasses slipping down his nose. He looked like he'd had a rough day and didn't even try to smile when he held out his credit card. “Coffee, medium.”

Gabriel took his card, punching in the order with practiced efficiency. “Room for milk?”

“Yes.”

And that was that. Or rather, that should have been that, but when Gabriel looked up again to hand the cup to the man, it was like he was shot in the chest. He actually staggered slightly, bumping his hip into the edge of the counter.

All the details he had missed at first glance jumped out now: a strong jaw and a straight nose, faint stubble and hair that was frankly ridiculous, long enough to curl slightly at the ends, but still somehow managing to work for the guy. Broad shoulders and a tapered waist, with muscles to die for likely hiding under all those layers.

Gabriel was completely blindsided.

The man took a sip of his coffee, then smiled a thanks. Gabriel made a small, strangled noise. He had _dimples_.

The man shot him a concerned look.

Gabriel shook his head.

The man lifted one eyebrow, then turned and walked straight back out of Gabriel's life. He looked just as good from behind as he did from the front, and Gabriel dropped his head on the counter with a groan.

* * *

**From Gabriel: I didn't ask for his number**

**From Gabriel: why didn't I ask for his number**

**From Gabriel: what if I never see him again???**

Castiel quickly grabbed his phone from his pocket and turned it off. Heat crawled up the back of his neck. Shit. He really should have turned his phone off before class had started, but Gabriel _knew_ he was working.

His students tittered as he cleared his throat and tossed his phone on his desk. “My apologies.”

“It's alright, Mr. Milton,” Jenny Turner said, smiling brightly—and flirtatiously—at him.

Jesus. This day was just getting better and better.

“Alright, class, as I was saying: while Marie Antoinette did not actually say ‘let them eat cake,’ France’s economic depression in 1789 was actually connected to poor harvests of grain, making flour a rare and precious commodity—”

When the final student trudged out of his class at the end of the day, Castiel turned his phone back on. Predictably, there were five new texts from Gabriel. He scrolled through them, then opened a new text.

**From Castiel: You know I have class.**

**From Gabriel: I’M HAVING A CRISIS**

Castiel highly doubted that, but he also knew his brother well enough that he wouldn't leave him alone until he at least pretended to listen to him vent.

**From Castiel: Are you still at Paradise?**

**From Gabriel: YES**

**From Gabriel: yes**

**From Gabriel: sorry**

**From Gabriel: caps were still on**

Castiel was thankful every day he had unlimited text messages. His phone bill would be horrendous because of just Gabriel alone.

Twenty minutes later found Castiel in Gabriel’s empty coffee shop, sitting on the old couch nestled between two bookshelves and sipping a steaming latte. Gabriel had been strictly forbidden to decorate Paradise Found, being unnaturally fond of checkered prints and red pleather. When he mentioned ‘palm trees,’ Castiel and Anna had been forced to step in. They kept it simple with white walls and teak furniture, but satisfied Gabriel’s need for the flamboyant with orange Chinese lanterns and pink throw pillows.

(This did not stop Gabriel from trying to rescue tacky decorations from thrift stores. Today it appeared to be a painting of an anatomically incorrect tiger prowling across a field. Castiel would need to smuggle it out when Gabriel wasn’t looking.)

“So you're in love with this guy. And you don't know his name,” Castiel said, dubiously.

“Haven't you heard of love at first sight?” Gabriel said, into the table.

“Since when did you, of all people, start believing in love at first sight?”

“Since it happened to me today, obviously."

“Okay,” Castiel said, with the infinite patience of a younger sibling with an older brother like Gabriel. “Does he even know you exist?”

Gabriel lifted his head enough to grimace at Castiel. “No? I mean, I gave him coffee. That has to mean something, right?”

“No.”

“He smiled at me.”

Castiel leveled a look at him.

Gabriel groaned and sagged back into his chair, dropping his head over the back. “No.”

“Well, I'm sorry then,” Castiel said, with what he thought was the appropriate amount of concern (none at all).

Gabriel straightened enough to scowl at Castiel. His expression flattened in a serious way that immediately put Castiel on edge.

“You're absolutely right," Gabriel said, thoughtfully. "I need to get his attention.”

Castiel’s eyes widened. “No. Whatever it is you're planning, don't do it. Gabriel, I'm _serious_.”

* * *

“What's that on your coffee cup?” Charlie asked leaning over Sam’s shoulder to peer closer at his cup. “'FOR A GOOD TIME CALL 555-493—' what the.”

Sam rolled his eyes, taking a long sip of his coffee. “It's the barista at Paradise Found. I think he's screwing with me.”

“Have you tried calling the number?” Charlie asked reaching for the cup.

Sam held it out of her reach and glared. “No. And I'm not going to. Calling will only encourage him.”

“Not interested?” Charlie asked, leaning a hip on the desk.

“Not at all.”

“Uh huh.”

Sam glared at her, draining the rest of his coffee in one swallow. “Don’t you have work to do? What do I keep you around for?”

“You keep me around because I’m the best,” Charlie sad, without any shame. She really was. Letting go of a paralegal like Charlie would be career suicide, and she used that truth on a daily basis.

“Does sending you to get me coffee fit in your job qualifications?”

Charlie looked outraged for all of the second it took her to manipulate the situation to her advantage. “Oh yes, definitely.”

“ _No,_ ” Sam said, belatedly realizing his huge mistake.

“What did you say this barista looks like?”

“Do you actually have something for me, or are you here for a social visit?” Sam asked, holding out his hand and ignoring her question.

Charlie smacked a file into his palm, smirking at him. “All right, Romeo. Here are your casenotes.”

She strolled out of his office and Sam dropped the file onto his desk. The Burns case wasn't going as well as he expected it to be. Their star witness, Ruby Benton, was—susceptible, and ready to jump sides on a whim. Charlie spent half her time chasing Ruby down to make sure she wasn't lured over to the prosecutor's side. Fucking Brady. He had absolutely no qualms with buying witnesses, and Ruby was only too willing to be bought. Sam thumbed through the top notes, twirling a pen between his fingers, and reached down to toss the cup into the trash.

He thought about the way the dim sunlight had hit the barista's eyes in just the right way to make them glint honey brown.

Sam put the empty cup on his desk.

* * *

The next day, Sam's cup said: SINGLE BARISTA SEEKING TALL DARK AND BROODY.

Charlie had laughed at him for five minutes straight.

* * *

Tall, dark, and broody didn't show up at Paradise for a whole week, long enough for Gabriel to decide he’d abandoned Paradise for a Starbucks and to work himself up into a surly funk. Meg had relegated him into the kitchens after he had gotten into yet another shouting match with one of his customers. One would think she was the owner, not him.

Gabriel was just bringing out a batch of brownies, fresh from the oven, when he heard the voice that made his heart do somersaults say, “Coffee, medium.”

“Room for—” Meg had started to say, before Gabriel pushed her out of the way, smacking the tray of still steaming brownies onto the counter.

“I got it, Meg. Why don’t you, uh, clean the espresso machine?” Gabriel said, pulling off his oven mitts to take his credit card. The look Meg shot him could strip paint, but Gabriel was made of stern stuff and just shooed her off with a wave of his hand.

Sam (and Gabriel maybe peeked at the name on his credit card) was watching them, one eyebrow raised and a tiny smirk curling at the corner of his mouth. It was a good thing Gabriel wasn’t the blushing sort, because he probably would have been bright red at his _totally obvious_ display just there.

Gabriel turned around to grab one of his special Sam-cups (today it read: YOU MOCHA ME CRAZY) and filled it with coffee. “Here you go, handsome,” he meant to say, with a saucy wink. He didn’t, though, because that would require more brainpower than he had these days.

Sam was looking down at the brownies with a small furrow between his eyebrows, like he wanted one but couldn’t figure out how to ask for it without breaking their silently agreed upon silence. Gabriel slid one of the brownies into a small paper bag and held it out to him. Sam opened his mouth like he wanted to protest, but then he took the bag and smiled his thanks.

Gabriel knew his smile in response was completely dopey, and continued to be dopey as Sam made his way to the cream and sugar station. A moment later, there was an extremely satisfying snort of laughter and Gabriel’s smile bloomed into an incredibly smug grin. Meg sidled up beside him, gaping incredulously.

“Oh my god, that was so _weird_ ,” Meg said, in mortified fascination.

“You shut up,” Gabriel said, snapping his towel at her.

“Was that _the_ Sam Winchester? The guy you’ve been pining over for the past month?” Meg whispered, way too loud for Gabriel’s peace of mind.

“Yes, shut _up_. He’s still here.”

“Is this like, a thing? Do you guys even talk?”

“We’re getting there,” said Gabriel, determinedly.

“I am so embarrassed for you right now.”

“ _Shut up_ ,” Gabriel hissed, grabbing the tray again. Of course, since he had just pulled it from the oven, it was still _really fucking hot_ and he immediately dropped it back on the counter with a small curse. Predictably, there was a beat of silence at the noise, before the conversations picked up again.

“Nice,” Meg said. Gabriel had no idea why he kept her around.

“Are you okay?”

Both Gabriel and Meg jumped slightly. The look Meg was shooting over Gabriel’s shoulder was a mix of horror and unholy glee, and Gabriel closed his eyes. It really wasn’t surprising at all that Sam was back at the counter, expression faintly concerned.

Of course, Gabriel’s brain-to-mouth functionality went completely on the fritz, and all he had to say was, “Ah.”

“He’s fine,” Meg said, grabbing Gabriel by the wrists to check his palms. He hadn’t held the pan for long enough to do any real damage, but it still stung. “He’s just being stupid.”

Sam grinned and Gabriel wondered if he should fire her. Something on his face must have shown what he was thinking because Meg smirked and shoved him none too lightly at the sink.

“Is there anything else I can help you with?” Meg asked and that? That was her flirtatious tone. He was _definitely_ going to fire her.

“No, I’m good. Thanks,” Sam said, pretty much quadrupling the number of words Gabriel had heard him say these past weeks, just in one conversation with Meg. Gabriel concentrated on running the water over his hands to keep himself from kicking his best barista in the shins. A moment later Sam made his way to the door. He held it open for Castiel, who was just walking in. Castiel stared up at him and awkwardly did not say ‘thank you,’ because that was his little brother in a nutshell.

Sam glanced over his shoulder at them before he left. Meg lifted a hand to wiggle her fingers goodbye. Gabriel smacked her hand back down again, then cursed in pain. 

"That was your fault," Meg said, distractedly. "I'll give it to you, Gabe. You do have good taste."

"I saw him first," Gabriel huffed.

"I don't think that matters," said Meg. Gabriel absolutely did not sulk. So it was possible the guy he had a big fat gay crush on was less of the gay and more of the tragically straight. 

“What happened to him?” Castiel asked, coming up to the counter and frowning at Gabriel.

“I ask myself that every day,” said Meg with a sigh.

Gabriel turned off the water and pointed at Meg. “You just earned yourself bathroom duty."

“Just because your love life is a three act tragedy doesn’t mean you get to be a dick,” Meg sniped.

Castiel’s eyes widened slightly and he glanced over his shoulder, as if he might catch another glimpse of Sam. “Wait. The guy at the door. Was that Sam Winchester?”

“The one and only,” Meg said, gleefully. “You realize loverboy is probably straight, right Gabe?”

“If I wanted your opinion, I would have asked for it.” Gabriel examined his hands, tentatively curling one into a fist. They should heal quickly enough, but he was going to be useless for the rest of the day. “Be useful and make Castiel a latte. I'm going to go put some burn gel on these.”

Meg rolled her eyes but dutifully went to the steamer. Castiel was all concerned eyebrows and Gabriel huffed, carefully tucking his oven mitts under his arm and making his way around the counter, to the kitchen.

Gabriel liked Paradise's kitchen. It was small, but the appliances were new and clean. If he had it his way, he would leave the shop in Meg's capable hands and spend the day baking. But they were still a fairly new shop and it was more efficient to get their pastries from vendors. Maybe one day, when he didn't need to worry so much about margins.

“You appear upset,” Castiel observed, cocking his head to the side. He had followed Gabriel into the kitchen and was leaning against the prep station, hands in his pockets.

“Blame it on the she-harpy.” Gabriel dropped the oven mitts on the counter and crouched down to pull the first aid kit out of one of the cabinets.

“I assume your master plan is not going well,” Castiel said, dryly.

“I'm slowly wearing him down,” Gabriel said, distractedly. He tore open a packet of burn gel and squeezed it onto one palm.

Castiel lifted an eyebrow.

“Very slowly.”

“Have you tried, I don’t know, starting a conversation with him?” Castiel asked, which was just rich coming from Mr. Socially Inept. The last time Castiel had tried to pick up a man, he had stuttered his way right out of a first date.

“I can do that,” Gabriel said, rubbing his hands together.

“Whatever you’re thinking, stop,” Castiel said, a little startled.

“Re-elax, Cas,” Gabriel said. “I can handle one conversation.”

“Do you _want_ to scare him away? I really would not recommend—”

“Excuse you, but I am the socially capable one in the room,” Gabriel said, which was mostly a lie. He wasn’t quite sure where their parents went wrong, but none of them were exactly _capable_ , not even Michael or Luci. Anna liked to say it was part of their charm.

“Fine,” Castiel said, narrowing his eyes. “This should be interesting.”

* * *

“So the barista keeps putting stupid notes on my coffee cups,” Sam told Dean later that evening. It had been a tradition to meet up at least once a week for food and drinks, and they’d just finished dinner and were nursing a couple of beers. It was still early enough that The Roadhouse was mostly empty, though a handful of regulars were starting to trickle in. Ellen was safely on the other side of the bar where she could not easily eavesdrop on Sam's newest drama. He loved the woman, but this was not exactly something he wanted to share with the class.

Dean’s reaction wasn’t much better than Charlie’s. He snorted unattractively into his beer. “Poor fucker probably doesn’t realize he’s crushing on the biggest prude in California.”

“Shut up. He's just punking me,” Sam sighed. He should probably find a different coffee shop. Paradise Found just happened to be on the way to the firm and served frankly awesome coffee and brownies to die for. There _was_ that Starbucks two blocks away…

“Seriously, though. Do you even know the dude’s name?”

“Gabriel.” The look Dean shot him in response was hugely skeptical and Sam leaned back, scowling. “He wears a nametag, you know.”

“So you looked.”

Sam glared. “He gave me his phone number. I was curious. Sue me.”

“You're the lawyer,” Dean said, drinking his beer smugly like that was actually a witty comeback. “Say, what time does Paradise Found close, anyway?”

“I think they stay open pretty late.”

“Think they’re open now?” Dean asked, checking his watch.

“Why?” Sam asked, immediately suspicious.

Twenty minutes and two shots of Jack later, they were standing in front of a mostly empty Paradise Found, both slightly tipsy. Probably that was why Sam deemed it an acceptable idea to bring Dean within twenty feet of the coffee shop.

“I don’t know why you insisted on coming,” Sam bitched, shoving his glasses into his hair.

“You said they had awesome brownies,” Dean said, as innocent as the purely driven snow.

Sam jabbed a finger at him. “Don’t you dare, Dean.”

“I have no idea what you’re talking about,” Dean said, pushing open the door to Paradise Found. The only customer was a scruffy haired man in a trenchcoat going through a stack of papers. He was distractedly twirling a red pen between his fingers, but he looked up when Dean and Sam walked in. He did a double take, then glanced back to the register.

“Hiya, welcome to Paradise Found—” Gabriel was saying, but he trailed off when he saw Sam. He glanced between him and Dean, then cleared his throat and pasted on a grin.

“Hi there,” Dean said, leaning against the counter. He flicked his eyes down at Gabriel’s name tag deliberately and added, “Gabriel. I hear you have some of the best brownies in town.”

Gabriel glanced at Sam again and Sam looked up at the ceiling, wondering if it would crack open so that he could be struck down by lightning. Or maybe Dean could be struck down. That would be infinitely more satisfying.

“You’ve come to the right place,” Gabriel said, cheerfully. “Would you like coffee with that?”

“Does it come with a special cup?” Dean asked, just as brightly.

Gabriel’s grin sharpened in a way that was completely new. It made Sam’s heart do a funny little twitch, which was also new and also _totally unexpected_. “For you, big guy? I’m sure I can dig something up.”

“Dean,” Sam hissed when Gabriel turned away. “You’re being a dick.”

“I’m just having some fun,” Dean muttered back, but rolled his eyes at Sam’s glare. “Fine, fine.”

Gabriel reappeared, holding out a coffee and small paper bag to Dean. Dean tsked when he saw there was no cheesy pickup line on the cup, but took it anyway.

“The usual?” Gabriel asked Sam after Dean wandered off to the milk and sugar station. He didn’t look as—as what? friendly? awestruck?—as usual.

Sam grimaced. “Ignore my brother. I try not to take him out in polite company, usually.”

“I heard that, bitch,” Dean called from the station.

Sam lifted his eyebrows as if to say: “See what I have to deal with?”

Gabriel’s grin relaxed from ‘I’m going to tear out your throat’ to ‘I understand your pain.’ “Oh trust me, I get it,” Gabriel said, flicking a glance over Sam’s shoulder. Sam followed his gaze to the scruffy haired man, who was glaring at Gabriel in an offended way.

“That’s your brother?” Sam asked.

“Yeah. Castiel,” Gabriel said, filling a cup of coffee and setting it on the counter.

“Ah.”

And that seemed to be the end of the conversation. Sam shifted awkwardly, then took his coffee with his usual grin. He shoulder-checked Dean on the way out the door and dodged a well-aimed elbow to the side.

“Way to be an asshole,” Sam snapped at Dean when the door closed behind him. “What the hell was that about?”

“Relax, Samantha,” Dean said as they strolled down the street towards Sam’s apartment. “I was just feelin’ him out. He obviously can take care of himself, no need to go all white knight to his damsel in distress.”

“That doesn’t mean you need to be a dick,” Sam gritted out.

Dean snorted and finished the rest of his coffee, then tried to toss it into a nearby bin.

It stuck to his hand.

“What the—" Dean said, shaking his hand. The ‘special’ coffee cup remained glued to his palm.

Sam threw his head back and laughed.

* * *

“That was a truly inspiring example of a ‘socially capable’ conversation,” Castiel said, smirking.

Gabriel threw the dish towel at his head.


	3. You Mocha Me Crazy

Whatever Sam was expecting that morning when he swung by Paradise for a cup of much needed coffee, it was not his older brother loitering just outside the sliding doors with an air horn in one hand and a roll of duct tape in the other.

“What are you doing, Dean,” Sam sighed.

Dean jumped and whirled around, with the same guilty expression from when they were kids and he'd crammed Lego blocks into the Impala’s vents. Sometimes, it was hard to believe Dean was the older one. Or that they were related at all. “Nothing! Nothing. Shouldn't you be at the firm?”

Sam glanced at his watch. “It's 6.”

“Early morning for you, eh?” Dean said.

“Not really.” The Burns case was going from bad to worse; Sam was putting in twelve hours at the firm and averaging four hours for sleep, and getting to the firm at 6:20 was becoming the norm. He adjusted his messenger bag (which was _not_ a man purse, no matter what Dean said). “What about you? Surprised to see you in the land of the living before 8.”

Dean glanced down at the air horn and the duct tape, then belatedly put them behind his back. 

“Very mature, Dean,” Sam said, judging.

“Do you know how long it took for me to get that damn cup off my hand? I'm just giving him back some of his own.”

“What’re you going to do?” 

“I was going to tape it under the toilet seat,” Dean grumbled.

It seemed harmless enough. Sam shrugged. Let Gabriel and Dean duke it out. Actually, this little war they had going on was—unexpected. From all the interactions Sam had with Gabriel, he’d pegged the other man to be shy. Slightly awkward. And then Dean had rolled in with his big mouth and even bigger attitude, and Sam had a feeling he was seeing the real Gabriel for the first time. He didn’t know what to do with that.

“Hey,” Dean said, a slow grin stretching across his face. “Want to help?”

“What? No. No way.” Sam held up both his hands, taking a step back. “I've got way too much stuff on my plate right now. Besides, I’ve been in prank wars with you. They never end well.”

“Come on, man! Aren't you always bitching about how he's screwing with you? All I need you to do is distract him,” Dean said. “It should be easy. Just like, flash some skin or something.”

“Are you pimping me out for your stupid prank?” Sam demanded, outraged.

“Yes,” Dean said.

“Absolutely not,” Sam said, firmly.

* * *

“So!” Sam said, overly bright. Gabriel blinked at him, taken aback. “What do you have on the menu today?”

“Uh,” Gabriel said, looking at the large chalkboard over his shoulder. It hadn't changed since Sam had started frequenting Paradise Found. “The usual?”

“Great! That's great.”

Gabriel leaned over the counter, immensely dubious. “Are you trying to distract me while your brother does something nefarious? Because if you are, the consequences will be many.”

Sam puffed out a breath. He really was shit at this subterfuge thing. “Would it help if I flashed some skin?”

Gabriel drew back, smug grin slipping away. His face smoothed out and something hard and hot crept into his eyes. Oh, wow. The back of Sam's neck warmed, but he didn't look away.

“Would you do it if I said yes?” he asked, a slow, _arrogant_ smirk curling the corners of his lips. Sam was saved by having to answer _that_ when Dean abruptly popped up behind his shoulder and successfully shattered the tense moment that was building between them.

“Hey there, Gabriel,” Dean said, flashing his toothiest grin.

“Hiya, bucko,” Gabriel said, all smiles again. “What’ll it be today?”

“I think I’ll try a mocha,” Dean said, leaning on the counter. He winked. “Better grab a brownie for the road, too.”

If Sam didn’t know better, he’d say Dean was _flirting_. When Gabriel turned away to make the coffee, Sam shoved Dean with a glare and a silent, _quit flirting with him, asshole_. Dean shoved back, harder, _don't shove me you gigantic dweeb_. Things sort of devolved after that, but by the time Gabriel turned back, they were standing side by side like two well-behaved children. 

Gabriel raised an incredulous eyebrow, sliding two cups over the counter. “Here you go, boys.”

“Thanks,” Sam said, apologetically. Dean grabbed him by the arm and dragged him bodily out of Paradise.

“I can’t believe I let you talk me into that,” Sam said. “What if he gets in trouble with his boss?” 

“He’ll be fine,” Dean said, distractedly holding up a hand. “Wait for it.” A minute later, they heard a sharp blast from the air horn, followed by shocked laughter from some of the customers. 

Dean cackled, smacking his hands together triumphantly. “That'll teach that Oompa Loompa to play a prank on _me_ ,” Dean crowed, then took a long drink from his coffee. 

He grinned smugly at Sam. 

Sam burst into surprised laughter.

Dean’s grin slowly faded into perplexed eyebrows. “What?” Sam just shook his head and pointed at the window. 

“Oh no,” Dean said, grimacing at the window. His teeth were a lollipop shade of blue. “I have clients today!” Dean shouted at the window. 

Gabriel cheerfully waved the air horn at him.

* * *

The next day, Dean cut out dozens of pictures of Nicolas Cage's face and stuck them into all of the books.

Gabriel put something _really bitter_ in Dean’s coffee.

Dean stuck a picture of an Oompa Loompa on Gabriel’s back.

Gabriel replaced the whipped cream for shaving cream in Dean’s mocha.

In the meantime, Sam slowly killed himself over his job, like the true adult.

* * *

Sam had stared at the file for a full minute before Charlie smacked it down on his desk and said, “Yeah, okay, we're taking a break.”

“What?” Sam said.

“No offense, Sam, but you are totally useless right now,” Charlie said, hauling him up by his arm. “At the very least, you need caffeine. And I can finally check out that coffee shop your boyfriend works at.”

“He's not my boyfriend,” Sam sputtered, but allowed himself to be pulled out of his office. 

Paradise Found was relatively empty when they got there, but they still had to wait in line behind a group of business people chatting about margins and ROI and other such foreign concepts. Gabriel had dialed his charm up to eleven and was laughing flirtatiously with a pretty Indian woman, leaning one elbow on the counter. Sam didn’t think she looked all that impressed, but then she smiled and reached over to touch the back of his wrist.

That was just fucking typical. Something bright and angry flared in Sam's chest. He wasn't sure why Gabriel chose to play with him like this, but clearly, that was all he'd been doing. Playing.

“Are you trying to murder them with your eyes or something?” Charlie asked, in a whisper.

“No,” Sam whispered back, but looked away.

Gabriel's eyes lit up when the business group stepped to the side and he noticed Sam and Charlie. “Well well. If it isn't my favorite customer. And who is this lovely lady?”

“My date,” Sam said, words tumbling out of his mouth without any input from his brain. Charlie snapped an ‘are you kidding me right now’ look at him and Sam glared back, before turning back to the register and saying, “I’ll have a coffee, med—” He trailed off, the words dying on his tongue.

Gabriel looked—he looked like he’d been slapped, one hand still frozen over the register. When Sam frowned at him, confused, he flinched a little and dropped his eyes back to the counter. 

“Coming right up,” he said, voice bright in a painful way, like the tinkle of shattering glass, and Sam thought, _oh_.

The rest of the order was completed in silence—not the awkward, shy silence of the past several months, but something more painful. That was not what Sam expected at _all_. He had been so sure this was one of Gabriel's practical jokes, that he'd been just trying to get a rise out of Sam. Gabriel flirted with _everyone_ , even Dean. But Gabriel wasn't looking either of them in the eye and Sam felt like the worst kind of jerk.

Charlie didn’t say anything when they left Paradise Found, but she didn’t need to. Sam was perfectly capable of ripping himself a new one. Stupid. Cruel. And people call _Dean_ the dick.

When she did finally speak again, it was to say, “You realize I'm a card-carrying lesbian, right?”

“I don't actually want to date you, Charlie,” Sam said, exasperated.

“Oh thank god,” Charlie exhaled, shoulders relaxing. “I mean, you're one of my best friends, for all that you're my boss, but—yeah. It just wouldn't have worked out. You have too many, um, pieces.” 

“Stop right there,” Sam said, holding up a hand. “I get it. I just—wanted him to stop screwing with me.”

Charlie picked at her brownie for a moment. “I don't think he was screwing with you, Sam,” she said, slowly. “He looked pretty upset.”

Sam rubbed his hands over his face. Shit really did come in threes. “He doesn't even know me,” Sam protested.

“So then why do you care? Just start going to the Starbucks,” Charlie said, shrugging. “Problem solved.”

Sam kicked at a rock on the sidewalk. It pinged off the side of a Honda parked on the street. He shoved his hands in his pockets and looked away, pretending like he hadn't just done that.

“Or,” Charlie continued, glancing at Sam out of the corner of one eye, “maybe you do care. If that's the case, you should apologize. You could have handled that better.”

“I know,” Sam groaned.

“You're pretty stunted, huh?” Charlie observed, then laughed and rubbed her arm exaggeratedly when he swatted her.

* * *

**From Meg: gabe hasn't been in for two days**

**From Meg: oh wait he's here**

**From Meg: shit**

**From Meg: FIX HIM**

Castiel really needed to get better at putting his phone on silent before class. His students tittered as he scrambled to grab his phone from his pocket, _again_. 

“Maybe you should leave your phone in the car, Mr. Milton,” Jo Harvelle said, smirking.

“That is an excellent piece of advice,” Castiel said, turning off his phone and putting it back in his pocket. He put aside his instinctive concern for now. School was over in twenty minutes. Meg _should_ be able to keep Gabriel under control until then.

“He's in the kitchen making brownies,” Meg said when he got to Paradise Found. It was late enough that the only customers were groups of students lounging outside to enjoy the unnaturally warm California night. “He got in a shouting match with a soccer mom who was complaining that her coffee was too hot.”

Castiel grimaced. Gabriel already didn't suffer fools gladly when he was in a good mood. The resulting argument must have been epic. “What happened?”

Meg snorted. “She demanded to speak to his manager.”

Castiel could just imagine how Gabriel reacted to _that_. 

“I ended up stepping in and pretending like I was his boss. She thinks I'm going to write him up.” She smirked and untied the back of her apron from around her neck. “Look, I've got to go. I've covered him for two days and I need a break. Can you make sure he doesn't single-handedly drive Paradise to the ground? I actually like my job, against better judgement.”

“Sure, Meg. Thanks for your help.” Castiel chewed on his lower lip, glancing at the kitchen. “Do you at least know what's put him in such a mood?”

Meg shrugged. “Don't ask me. Whatever happened, he's not talking about it.” She grabbed her keys and cellphone from under the counter in a blatant disregard to Gabriel's rules and tossed a wave to Castiel. “Good luck.”

Castiel walked over to the kitchen, pushing open the door and hesitantly peering in. “Gabe?” 

Gabriel was covered from the elbows down with flour and was kneading dough with a concerning amount of violence. He glanced up, wiping his forehead with the crook of his elbow. “Hiya, Cassie.”

Castiel really hated that nickname, but he let it slide. Gabriel only called him Cassie when things weren't good. “Meg left for the day.”

“Great,” Gabriel said, thumping both his fists down on the dough. “Who gave her the right to take off before her shift was up?”

“She did cover you for two days.”

Gabriel dusted the flour off his palms ineffectively. He didn't respond, just left his dough on the prep station and brushed passed Castiel to wash up in the large sink, before heading back into the shop.

“Gabe,” Castiel said, following him. He leaned against the counter, next to the espresso machine. Gabriel looked—bad. He was still cleanly shaven, but he was pale and had dark circles around his eyes, and a streak of flour down one cheek. “What happened?”

“Nothing.”

Castiel was fully cognizant of Gabriel’s bullshit tone. He frowned at the stiff set of Gabriel's shoulders. It didn't take long for Gabriel to break; he really wasn't good at silence. 

“He brought a date here, alright? Some pretty redhaired girl.”

Well, shit. Castiel had no idea how his brother—who was confidant to the point of arrogance—managed to get himself so messed up over a guy he didn’t know from Adam.

“You were already aware he was likely straight,” Castiel said, cautiously. 

Gabriel didn’t answer, just grabbed a towel and began methodically cleaning the espresso machine. Castiel sighed through his nose. “I don't get it. You don't even know this guy. How did he get to you like this?”

“I don't know,” Gabriel said, loudly. “I have _no_ idea. He walked into Paradise, and I just knew. That's the one.”

Castiel shook his head. “That's not like you at all.”

“You're telling me,” Gabriel said, deflating. He swiped the towel over the tray grate in a desultory fashion.

“There are other men out there,” Castiel tried, awkwardly. Honestly, he was so bad at this stuff. Even Luci was better at sympathy than he was.

Gabriel snorted. “Stop, before you injure something.”

“I am only trying to help,” said Castiel, stiffly.

“I know, I know. Just—”

The bell over the door tinkled and Castiel was surprised to see Sam Winchester walk in like a bad joke. He had some nerve, coming back to Paradise as if he were _welcome_. Castiel turned back to Gabriel to see how he was handling this new development.

Gabriel had disappeared.

Or rather, Gabriel was crouched on the floor, staring up at Castiel with wide, desperate eyes. Castiel gaped back at him. What the hell. He had no idea how to run the register—or any other machine in the coffee shop, for that matter.

“Uh, hi,” Sam said, when he got to the register. This close, Castiel could see he wasn't much better off than Gabriel. He looked exhausted, skin dark under his eyes, and a little pissed off. Castiel folded his arms over his chest unsympathetically and Sam grimaced.

“What,” Castiel said, flatly.

Sam glanced around the shop as if looking for something (or, more likely, someone). “I was just—” He stopped and took a breath. “I wanted to order something.”

There was a long moment where Sam and Castiel just stared at each other, like Sam had just spoken in a completely different language and Castiel was trying to puzzle him out. “You want to order something,” Castiel repeated, flatly.

“That's usually what you do at a coffee shop,” Sam said, dryly.

“Right.” This was just—great. Castiel resisted the urge to glare down at Gabriel.

Sam leaned over the counter slightly to peer at Castiel's face, and Castiel felt Gabriel crowd closer to the counter, bumping his elbow into Castiel's calf. “Aren't you Gabriel's brother? I didn't know you worked here.”

“Oops,” Castiel said, deadpan, and then deliberately knocked a pen off the counter. 

In a series of desperate shrugs and raised eyebrows, he told Gabriel: _I have no idea what the hell I’m doing._

Gabriel rolled his eyes and silently jabbed a finger towards the button on the coffee maker: _You push a fucking button, you mook._

“Please,” Gabriel mouthed.

Castiel scowled, but stood up, straightening out his shirt. “What do you want.”

Sam looked about as impressed as Castiel felt. “I’ll have a mocha.”

“We’re out,” said Castiel.

Sam folded his arms over his chest. “Then I’ll take a latte.”

“Out,” said Castiel.

“You’re out of milk?” Sam asked, raising his eyebrows.

Castiel shrugged.

Sam sighed, dropping his arms to his sides. “Where’s Gabriel? I swear I saw him before I came in.”

Castiel flicked a quick glance down. When Sam said his name, Gabriel flinched like his heart was breaking all over again. Castiel briefly entertained the idea of punching in Sam’s perfect nose, but Gabriel would be even more devastated if his health score went down because Sam bled everywhere.

“You can have a coffee,” Castiel said, threateningly.

Sam didn’t look very impressed. It wasn't a very impressive threat. Also, Sam towered over Castiel by about a foot and a half. Castiel just lifted a challenging eyebrow and Sam sighed, deflating. 

“Okay.”

The rest of the transaction was done in tense silence. Twice Castiel had to stop himself from throwing the coffee in Sam's face. Instead, he thunked it down on the counter harder than necessary. Sam tossed his card down on the counter in response. Castiel punched some buttons and pretended to ring him up, then tossed the card back on the counter.

Sam took the cup, frowning at it as if it disappointed him somehow, and then looked up at Castiel. “Can you tell—”

“I don’t think you realize how lucky you are that I haven’t punched you in the face yet,” Castiel said, flatly.

Sam’s jaw clenched and for a moment it looked like he was considering throwing the coffee in _Castiel’s_ face. He nodded once, tightly, and left the shop. There was a sound of tinkling bells, and then the shop was silent. Castiel glanced down. Gabriel had his forehead pressed against his knees, and Castiel dropped his hand to the top of his head.

“I am such a mess,” Gabriel sighed.

* * *

It went like that for another two days. Each time Sam popped into the shop, Gabriel was nowhere to be seen. The brunette he’d seen work the register a few times—Meg, her nametag said—always looked at him with a mix of anger and pity. 

“Look, Sam,” she said, after Sam stopped by the coffee shop for the second time that day, during lunch. She glanced over her shoulder at the kitchen door, then leaned forward. “I think you’re a complete asshole.”

“Thanks,” Sam said, unhappily. “I’m trying to make it better.”

“I know,” Meg said. “That’s why I’m telling you this. He’s closing tonight. Alone.” She looked at him meaningfully.

“Thank you,” Sam said.

“Don’t fuck this up,” Meg said.

He ended up getting sucked into a spiral of paperwork and phone calls back at the firm, and by the time he glanced at the clock again, it was 8:55 p.m. Paradise Found closed at 9. He rushed out the door, snatching up his coat from the armrest of his couch. By the time he’d finished locking up and all but sprinted to Paradise Found, it was already 9:20.

Sam hung back, away from the windows. There were still lights on in the shop; Gabriel was probably finishing cleaning up. Sure enough, Gabriel stepped through the door five minutes later, locking the door behind him with a huge ring of keys. It was the first time Sam had seen him out from behind the counter and in something other than his regulation black apron and white button up. He seemed somehow more _real_ in his green jacket and blue jeans.

Gabriel turned away, twirling the keys on his ring finger, and Sam jerked forward. “Gabriel, wait.”

The keys whizzed off Gabriel’s finger and into the middle of the street, and Gabriel whirled around, shocked. Whatever reaction Sam had been expecting, it wasn’t that. He hurried into the street to pick up the keys, then made his way back to Gabriel, cautious.

“Uh,” Gabriel said, looking at the keys, then into Sam’s face. Without the counter between them, their height difference was more obvious. “Thanks.” He held out his hand.

Sam caught the keys in his fist and held them out of reach. 

“Seriously?” Gabriel asked, glaring up at Sam. It was childish, but if Sam gave Gabriel back his keys, he would probably sprint away in the opposite direction, never to be seen again.

“I just want like, five minutes to talk.”

“Fine,” Gabriel snapped. There was a beat, then he lunged up to swipe at them again. Sam jerked them out of the way. Gabriel's glared stormily at him. “You are the _worst_.”

Gabriel’s attempt left scant inches between them. Sam looked down into Gabriel’s eyes and said, seriously, “I was a dick. I’m sorry.”

For a heartbeat, Gabriel stared back up at him. Then he pushed his hands into his pockets and shrugged, taking a large step back. “What’s there to be sorry about? I can read the writing on the wall. I know when to back off.”

“I thought you were fucking with me,” Sam said.

“And now that you know I’m not?” Gabriel asked. When Sam didn’t say anything, his lips twisted into an unhappy smirk. “That’s what I thought.”

Something important was slipping from between his fingers, but he didn’t even really know what or how to stop it. “Can’t we—can’t we be friends?” Sam asked. 

“Sam, Sam,” Gabriel said, shaking his head. He leaned forward, conspiratory. “I don’t want to be your _friend_.” His voice was hard, sharp, and with that same intent from several days ago. Sam pressed his lips together, breath caught in his throat.

Gabriel held out his hand, silently. Sam exhaled through his nose and dropped the keys onto his palm. “See ya,” Gabriel said, and then walked away.

Sam watched him go, clenching his jaw. He took a step after Gabriel to—to do what, he didn’t know—when his phone rang.

It was Dean. Sam scowled down at the screen, then sent the call to voicemail.

* * *

_”You have reached the voicemail of Sam Winchester—”_

Dean glared down at his phone, then punched the end button. Bitch sent him to voicemail _again_. He’d been trying to get ahold of his brother since yesterday night. He knew Sam was in the middle of some big case or something, but it was _Saturday_ and wasn’t like Dean was calling just to shoot the shit. He opened a new text.

**From Dean: Call me asap**

When Sam didn’t call back in the next ten minutes, Dean cursed under his breath, grabbed his keys from his desk, and stalked out of his office. He needed a beer.

Singer & Winchester Auto Shop was a bustle of activity: they were backed up by at least five cars. Outside, there was the steady chatter of drills and running motors, with Led Zeppelin singing about Mordor in the background. As co-owner and one of the lead mechanics, Dean should be working, instead of stomping over to his own Impala.

“Hey, Winchester!” Bobby shouted from behind a ‘95 Tacoma. “Where the hell are you goin’ boy?”

“Lunch at The Roadhouse,” Dean shouted back, shouldering on his leather jacket. Bobby frowned down at his watch, then back up at Dean. “Cool it, old man. I got urgent family business.”

“At The Roadhouse?” Bobby asked, disbelieving.

“Yeah,” Dean said, because it was true. 

Bobby seemed to remember just who he was speaking to, because he sighed with gruff concern. “You let me know if you need anything, okay?” 

“Sure, Bobby.”

He tried calling Sam again on the road, but wasn’t surprised when his call got sent to voicemail, again. That was just fucking typical. He thumbed through his contacts until he found Charlie Bradbury’s number, but hesitated, and then locked his phone again and tossed it into the passenger seat.

“Woah,” Jo said, when Dean stomped in. “You look like you need a drink.”

“Are you even old enough to be behind the bar?” Dean asked, dropping onto one of the stools.

Jo rolled her eyes. “Do you want a beer or not, Grandpa?”

“Better make it two.”

It was Ellen who came back with his drink. She set the bottle in front of him and leaned against the bar. Dean chugged half his beer down in one go and Ellen raised her eyebrows, leaning against the bar. “Tough day, sugar?”

“Tough news,” Dean corrected.

“Want to talk about it?”

“Nah,” Dean said. “Later. Gotta talk it out with Sammy, first.”

She nodded, reaching over to clap Dean on the shoulder comfortingly. “You let me know if you need anything, you hear?” He smiled gratefully at her, but it immediately fell away when she drifted off to another customer. 

He had no idea what he was going to do. Dean was self-sacrificing to the point of stupidity when it came to family, but this? This was something entirely different. This was _life-changing_. He sighed and thunked the bottle down. 

There was a redhead sitting by herself at the other end of the bar. She glanced at him from the corner of her eye, then looked back down. Well, well. Dean could use a distraction. He took a swig from his beer, then got off his stool and strolled over to her.

“Hey there,” he grinned. “What's a pretty girl like you doing by yourself in a bar like this?”

The girl smiled uncertainly at him and opened her mouth to respond, when a voice like fingers sliding through gravel interrupted. “She's not alone.”

Dean turned around to find a man with fuck-me black hair and a bottle of beer in each hand. His amused, slightly annoyed expression faded and the brightest blue eyes Dean had ever seen abruptly narrowed. Dean's own smile faltered. The guy looked—familiar. And really fucking pissed off. 

“ _You_ ,” the guy snarled.

Blue Eyes looked like he was itching for a fight. Dean's lips curled into an arrogant smirk. He had no idea what he did to piss the guy off so badly, but Dean didn’t have the capacity for this right now. He was having a bad week.

“Sorry, sweetheart, do I know you?” Dean asked, leaning against the bar. “I’m pretty sure I’d remember eyes like those. Or an ass like that.” He peered around the man for a better look, whistling lowly through his teeth.

The guy’s eyes widened and he took a step forward. “You conceited, _arrogant_ —”

“Yeah, baby, I get all tingly when you insult me with multiple syllables.” 

“Castiel,” the redhead said, warningly.

Dean grinned a little wildly, shoving away from the bar. He crooked his fingers at this Castiel guy, beckoning. “Come on, cupcake. Let's dance.”

Castiel dropped both bottles to the floor, took two steps forward, and slugged Dean across the face.


	4. Interlude

It had taken the cupid longer than he'd anticipated to finish the his job, but it was _done_ and he could finally get back to what he loved doing best. Where has he left off? Ah, yes—the Miltons and the Winchesters. 

He wondered how Gabriel and Samuel were, if the two lovebirds had gone on their first date yet. Or perhaps they had already moved in together! Though humans were oddly stubborn when it came to love, preferring to drag out their little courtship rituals. The cupid didn't always like or understand the games humans played, not understanding why they would choose to toy with the ones they loved. But Samuel and Gabriel were soulmates! Surely everything was fine.

* * *

Gabriel Milton was sitting cross-legged on a red pleather couch, washing down a pint of vanilla ice cream with a bottle of red wine and tearily browsing through dog rescue sites on his laptop. 

It was—not exactly the scene the cupid had expected to come upon. The cupid frowned at Gabriel's mark. What he saw made his gasp, a hand flying up to his own chest, where his vessel’s heart was. The mark had _faded_. But how could that be? The cupid’s sigil only disappeared if—if—

If one lover spurned another.

The cupid flashed over to Sam's home. He _knew_ he shouldn't have left his job half-finished! If they would have given him three lousy minutes, he could have finished the job, and Sam and Gabriel would have had their happily ever after. Now Gabriel was eating away his feelings and Samuel Winchester—

Samuel Winchester was sitting at his desk, hands buried in his hair and staring down at a stack of papers with wide eyed resignation. He had not slept for two nights, trying to salvage the case he was going to lose, but too distracted. He was _miserable_.

For the first time in his long career, the cupid doubted. Was it possible for two souls who were made for each other to fight destiny?

What in Heaven _happened_?

The cupid left Samuel to his files, flashing over to his next mark. He found Castiel Milton, unexpectedly, at a bar. He appeared to be in the middle of a fight with, even more unexpectedly, Dean Winchester.

“It’s not my fault your brother is a desperate weirdo,” Dean snapped. Castiel’s eyes widened and he lunged at Dean, but Castiel's sister, Anna Milton, clung to one of his arms with both her hands.

“Yeah, well, your brother’s a dick!” Castiel shouted. 

“Why are you hitting _me_ , then?” Dean shouted back, rubbing his jaw. 

“You're a dick, too!”

The cupid cringed. This was wrong wrong wrong. The two souls had met, had recognized each other, and had reacted. Their blood ran hot for each other, but they were both filled with such anger that the passion had translated into violence. 

The cupid shook his head in despair. How did it get this bad? Even without the mark, the two couples should at least tolerate each other.

He would have to monitor the situation further. Marking them now would just end in disaster.


	5. I Like You a Latte

So _this_ was hell.

Not only had Sam had to haul Dean’s dumb ass from the Roadhouse after he’d gotten into a barfight with _Gabriel’s brother_ , but before Sam could even digest that juicy tidbit, Dean had dropped a much larger bombshell while angrily bleeding all over Sam’s car. And while Sam was desperately trying to sort out that fun whirlwind of family drama, Ruby cheerfully sold herself to the prosecutor’s side.

And then Sam lost the Burns case.

He had already known it wasn’t going be salvageable, but somehow it still felt like a personal betrayal when Ruby flashed a cherry-red smile at him and wiggled her fingers in a sardonic apology from the other side of the courtroom. Sam’s totally healthy response to this outcome was to get completely bombed, alone, in his apartment.

He was self-aware enough to recognize that losing the case wasn’t the only thing responsible for the yawning pit in his chest, but he just didn’t understand _why_. Why did he care whether or not some ridiculous barista liked him or not?

“You look like shit,” Dean informed him the next morning, after he’d barged into Sam’s apartment at the ass crack of the morning with a greasy bag that smelled like toasted bagels. Sam didn’t even bother lifting himself from where he’d faceplanted onto his couch last night when the booze finally did him in.

“Thank you, Dean,” Sam said, around a mouthful of couch cushion.

“You smell like shit, too,” Dean said, and Sam could practically hear the delicate nose wrinkle to his voice.

Sam shifted into a sitting position, raking his lank hair out of his face. He accepted the paper bag from Dean, pulling out a three cheese bagel slathered with jalapeno cream cheese. “What are you doing here, anyway?”

“I heard about the Burns case. Charlie told me you took the day off.” Dean settled himself on the coffee table and Sam handed the bag back to him. “Sorry, man. I know that case meant a lot to you.”

Sam carefully unwrapped his bagel, scooping off some of the cream cheese with his finger. They always put way too much.

“Or,” Dean drawled, his eyebrows suspicious, “not.”

“No, it did.” The case _had_ meant a lot to him, but mostly—if he was being honest with himself—because he really hadn’t wanted to lose to _fucking Brady_.

“Wait a minute,” Dean said, setting his bagel to the side so that he could properly glare at Sam. “Tell me you ain’t actin’ all emo-teenager because of _Gabriel_.”

“I’m not emo,” Sam snapped reflexively, then shoved a bite of bagel into his mouth before he could say anything incriminating.

Dean scoffed rudely, like he thought Sam was a big fat liar. “When was the last time you went to Paradise Found?”

Sam considered. With the shitshow that had become his life, he’d sort of lost track of time. “I don’t know, a week ago? Whenever I had to drag your ass out of the Roadhouse.”

“Two weeks ago,” Dean said, then whistled. “Man, you must be really hard up right now.”

Sam ripped off another piece of his bagel. “There is nothing between Gabriel and me.”

Dean chewed judgmentally at him.

“What?” Sam snapped.

“Do you want there to be?” Dean asked, not even bothering to swallow before he spoke because he was a goddamn animal.

Sam wasn’t the kind of jerk who craved attention so much that as soon as he stopped getting it, he threw a fit. And yet now that Gabriel had basically told Sam to piss off, all he could think about was the way Gabriel’s lips twitched in a mischievous smile or how the ends of his hair curled at the base of his neck. Okay, so maybe he was _exactly_ that kind of jerk.

“Okay, enough,” Dean said, judo chopping the air in front of Sam’s face, as if Sam’s thoughts were a physical thing. “I could practically see you going all chick flick on me. Gross.”

That last bite of bagel Sam had taken stuck uncomfortably in his throat. “I am so fucked.”

“Dude. Too much info,” Dean said, revolted.

Sam threw his crumpled bagel wrapper at Dean’s face.

Dean caught it and threw it back. His aim was better, much to Sam’s annoyance. “Not that I understand how you could possibly have a thing for that tiny jerkass—good taste is clearly _not_ genetic—but maybe you should nut up and just ask the little troll out. On a date.”

“I don’t know, Dean,” Sam sighed, slumping back into the couch. “I’m pretty sure he wants nothing to do with me. I screwed things up pretty royally the last time we talked. Two _weeks_ ago.”

Dean coughed into his fist something that sounded an awful lot like, “Pussy.”

Sam glared at him. Dean stared right on back at him, tearing off pieces of his bagel and chewing with deliberate patience.

“Fine. Fine!” Sam shoved off the couch and stomped towards the door. If he was going to do this, he had to do it now, before he lost his nerve.

Dean leaped up from the coffee table. “Wait, you’re going right now? Looking like that? _Smelling_ like that?”

“Yeah. Lock the door when you leave.”

“Like I’d miss this,” Dean said, tossing his bagel wrapper on the coffee table. “Let’s go.”

* * *

Love at first sight or no, Gabriel Milton pines for _no man_. So when Sam Winchester pushed into Paradise Found (after being MIA for two weeks and smelling like a bar counter) trailed by his loudmouth brother, Gabriel plastered on his best smile and said, “Welcome to Paradise Found. How can I help you?”

“Oh my God,” Dean said. “He’s been replaced by a pod person.”

Gabriel’s smile sharpened. “Watch it, big guy. You are on thin fucking ice right now.”

“What did _I_ do?” Dean asked, offended.

Gabriel rolled his eyes. “Castiel?” he reminded him.

“I didn’t do Casti—oh.” Dean folded his arms over his chest, jutting his chin out. “He started it.”

“Which is why you’re not out on your ass right now,” Gabriel informed him, with infinite patience. “One of his students called the battered spouse hotline for him.”

Dean’s lips were twitching, a mix of horrified and inappropriately amused, and Gabriel dismissed him, turning back to Sam. Sam looked completely exhausted, the skin under his eyes thin and purple, his normally fluffy hair lank and flat on one side. His clothing was rumpled, like he’d just fallen into bed after a long night of drinking. Gabriel viciously squashed that little twinge of concern. It wasn’t his place. He’d been shot down romantically by Sam and he’d shot down Sam’s overture of friendship. Which left them as nothing more than barista and customer.

He could do this.

The small gaggle of regulars that recognized the Winchesters from the Great Dean vs. Gabriel Prank War leaned forward eagerly for the newest episode of the sitcom that was Gabriel’s life. Gabriel was almost sorry to deprive them of the show.

“What can I get you?” Gabriel asked politely, once again the perfect barista.

Sam looked slightly taken aback. “I’ll have—the usual?” When Gabriel just smiled blankly at him, he hurriedly added, “A medium coffee.”

Gabriel turned to the coffee maker, his expression cracking. Normally he would never celebrate driving a customer off to a competitor, but after two weeks he’d resigned himself to the fact that Sam had fucked off to the Starbucks down the street. And he’d been _okay_ with that. Really. He filled the cup to the brim, even though he damn well knew Sam liked room for milk, and set it on the counter.

“That will be one-fifty,” Gabriel said, pleasantly.

Sam flinched, but dutifully pulled his wallet out from his back pocket. “Gabriel, listen—“

“Cash only for orders under five dollars,” Gabriel interrupted.

Sam’s eyes narrowed. “I’ve always paid with card.”

“It’s a new policy,” Gabriel said, lying remorselessly. “Trying to cut back on fees, and all.”

Sam’s eyebrows furrowed, but he dug out a couple of bills. He sucked in a deep breath. “Ga—“

“We only accept bills from the year 2000 and up,” Gabriel bleated, jabbing a finger at one of the bills. “That one’s from 1997.”

Dean snorted loudly, then cleared his throat when Sam and Gabriel looked at him. “Sorry. Please, continue. This is almost as entertaining as Dr. Sexy.”

“Dean, shut up,” Sam snapped, then turned back to Gabriel, rolling his eyes. “You can’t do that, Gabriel. Lawyer, remember?”

“You’re a lawyer?” Gabriel’s traitorous mouth said. Actually, he _hadn’t_ known that. It explained the exhaustion. He snapped himself out of it and tightened his smile. “No, you’re right. But I _do_ have the right to deny service to anyone for any reason.”

“Dude,” Dean said. “That’s cold.”

“You would deny me service?” Sam’s eyes widened like he was some sort of heartbroken puppy.

“No, no,” Gabriel gritted out, hating himself for how quickly he relented. He snapped impatiently. “Just give me the freakin’ cash, Sam.”

He rang him up in silence, Sam thankfully giving up for the time being. When Gabriel deliberately set the change on the counter to avoid touching Sam’s hand, Dean plowed his elbow into Sam’s ribs.

Sam snapped a glare at him, then braced himself against the counter with one hand and leaned closer. “Hey, can we talk? Do you have break soon?”

“No can do, Sammy,” Gabriel said, snatching up a brownie with a pair of tongs and tossing it on a plate. “Looks like I have a full schedule.”

“Don’t call—“ Sam said, knee-jerk, then shook his head quickly. “Five minutes. I promise I won’t bother you again if you give me five minutes.”

Gabriel hesitated by the counter flap. There was a small kindling of hope starting to burn in his stomach. Was he being too stubborn? It wouldn’t be the first time Gabriel dug his heels in about something to avoid getting hurt. Further.

He shoved the flap up and viciously squashed that little flame of hope, too. This was exactly why he _didn’t_ let himself be vulnerable. “I think we’ve said everything that needs to be said two weeks ago, Sam,” Gabriel said, still with that fake smile plastered all over his face, and scurried over to the one person in the coffee shop that wasn’t watching the soap opera unfold with voyeuristic glee.

The suit plucked his headphone out of his ear when Gabriel appeared beside him, eyebrows furrowed in confusion. “I didn’t order a brownie.”

“On the house,” Gabriel said, grumpily dumping the plate onto a stack of important looking documents, and then whirled into the kitchen to hide for the rest of his miserable life.

* * *

Sam glowered at the man, who frowned down at the brownie like he wasn’t sure what to do with it. He jumped when a sharp finger jabbed him in the ribs.

“Don’t eat the guy just because Gabriel gave him some sugar,” Dean said.

“Dean,” Sam growled. “That was a monumental failure.”

“Dude. It was _epic_ ,” he agreed.

Sam sighed, shoulders slumping. “I guess that’s it then.”

Dean stared at him in disbelief. “You’re giving up. Just like that.”

“I’m not going to harass the guy into a date,” Sam shot back, grabbing his coffee from the counter and stalking to the door. “One, I’m not that desperate. Two, that’s just gross.”

Dean jogged in front of him, pushing the door open. “Whatever happened to fighting for the ones you love?”

“Dean,” Sam said, seriously. “I’m not in love.”

“But you _want to_ be.”

Sam thought about the way Gabriel’s honey brown eyes lit up with mischief during his prank war with Dean. Or when he smiled at Sam—not that cold, thin smirk, or the plastic customer service grin, but the warm curl of his lips early in the morning, like he was always happily surprised whenever Sam walked into Paradise Found.

“Maybe,” Sam admitted.

Dean threw his hands out in disbelief. “Then why the hell are you just bitching and moaning? _Do something_ about it.”

“I’m not sure I should be taking romantic advice from you,” Sam said.

“Hey man, at least I’m getting laid and not crying to My Chemistry Romance every night.”

Sam didn’t bother to correct the butchered band name. He just shoved his cackling brother into the (relatively) empty street.

* * *

Castiel hesitantly pushed the door to Paradise Found open. His phone had been ominously quiet all day, which set off all sorts of alarm bells. Usually Gabriel sent him at least three texts by eleven a.m. He was probably being overprotective, but he couldn’t shake the feeling something bad had happened. After Gabriel ignored the second funny bird gif Castiel texted him that night, he gave in and made his way to Paradise Found.

The coffee shop was empty by the time Castiel rolled in, save for Gabriel, who was wiping the counter in a desultory manner. Castiel locked the door behind him, even though the shop was technically open for another fifteen minutes.

“Gabe?” Castiel said, hesitantly.

Gabriel looked up, one corner of his mouth ticking up into a fragile smile. “Oh. Hey, Castiel.”

Castiel’s stomach clenched. There was something weirdly muted about his brother, like all of his buzzing energy and love for life had been carefully bottled up and stored away. “Are you okay?”

“Yeah, I’m good,” Gabriel said, in a very _not_ good voice.

“Bullshit.”

That caught Gabriel’s attention and he smiled for real. “There’s a reason why you’re my fav, Cassie. Always so upfront.” The small glimmer of happiness faded and his shoulders slumped. “I don’t know. I just—feel like I’m losing something.” He sighed. “My mind, maybe.”

“Did something happen?” When Gabriel said nothing, just swiped his rag across the clean counter, Castiel guessed, “Sam.”

“Tweedle Dee and Tweedle Douche did come in today,” Gabriel said, not looking up.

Castiel cursed silently. Gabriel had been doing so much better in these two weeks. If Sam would just keep his distance, maybe Gabriel could fully move on. As obnoxious as his older brother was, Castiel had always kind of hero worshipped him and it was nearly impossible for him to see his giant of a brother diminished like this. He clenched his fists, hating how helpless he felt.

“Hey.” Castiel looked up to find Gabriel smiling at him. Comforting _him_. “Really. It’s okay.”

“Sam’s a fucking idiot,” Castiel snapped.

Gabriel chuckled. “He’s in good company.” He swung his towel over his shoulder and circled the counter, resting his hand on Castiel’s shoulder briefly. “Don’t worry so much. You’ll get wrinkles.”

“Where are you going?”

“Just going to load the dishwasher,” Gabriel said, his lips still curved in a brittle smile.

Castiel knew his older brother well enough to recognize when he wanted to be alone. He watched him go, noting the defeated slump to his shoulders. He kind of felt like punching something—or some _one_ , like Sam Winchester, who was currently staring into Paradise Found like some sort of lovesick puppy, what the fuck.

Castiel rushed to the door before Gabriel came back into the coffee shop, not wanting to his brother to see the object of his misery. He shoved outside, then shoved Sam in the chest. Sam, much to his annoyance, didn’t even stumble.

“Haven’t you done enough?” Castiel demanded, poking Sam on the chest again.

Sam raked his fingers through his hair, frustrated. “Look, I know Gabriel never wants to see me again, but—can you just give him this?” He fished out a cream colored envelope from a pocket inside his coat and held it out to Castiel.

Castiel didn’t take it. “Why the hell should I?”

“Because,” Sam drew out slowly, “I am trying to _fix this_.”

“With Hallmark?”

There was a flash of uncertainty in Sam’s eyes that, amazingly, made Castiel hardened heart soften. Just a little. “Yes?”

Castiel glared at the card, then back at Sam. Then he snatched the card out of Sam’s hand. “If you mess this up more than you already have—“

“Yeah, yeah. You’ll gut me and leave out my remains as an example,” Sam said, waving a flippant hand, which—was way more colorful than Castiel’s intended, “I’ll beat you up!”

“Right,” Castiel said, a little faintly.

“Thank you, Castiel,” Sam said, earnestly. Castiel stared at him without responding, then went back into Paradise Found and slammed the door in Sam’s face.

Gabriel popped back into the shop just as Castiel stomped back in. He cocked his head to the side, drying his hands on his rag. “What’s up, baby bro?”

“Delivery,” Castiel said, flipping the card towards Gabriel. “From Sam.”

Gabriel caught the card, then dropped the towel on coffee table. Castiel settled himself behind Gabriel’s shoulder to better read the card and ignored the fact that this was clearly a personal missive. Gabriel tore open the side of the envelope.

On the front of the card, two cutesy cartoon coffee cups bumped into each other, little hearts floating over their Disney faces. Scrawled at the top of the card in aggressive magenta were the words: I LIKE YOU A LATTE

Gabriel flipped open the card, his fingers trembling slightly.

_Gabriel—_

_We got off on a monumentally bad start, mostly because I am a giant oblivious dick, for which I am truly sorry. If you can find it in yourself to forgive me, I’m hoping we can start over. Maybe with dinner and a movie?_

And, because Sam was a sarcastic little shit, he’d added: _Check yes or no_ with two checkboxes below.

“Gabe?” Castiel asked, tentatively.

Gabriel shoved the card back into the envelope, dropped it onto the coffee table, and stormed into the kitchen.

* * *

Sam paced in front of Paradise Found, hands shoved into his pockets. This was it. If Gabriel rejected him, he’d—well, he’d start going to Starbucks, for one. The card hadn’t been big or grand like Charlie had suggested when he’d asked for advice, or sexual like _Dean_ had suggested, but it somehow felt fitting. Which probably meant it was totally lame. Sam groaned at the sky and pressed the heels of his hands into his eyes. This had been a _stupid_ plan. Why couldn’t Gabriel be uncomplicated, like all the women Sam picked up?

His head snapped down hopefully when the bells over the door jangled, but his shoulders sagged when Castiel stepped out, looking like a put upon thundercloud.

“He’s throwing a fit,” Castiel explained.

Sam winced. Well, at least he had his answer. Then he realized Castiel was holding the door open for him, head cocked expectantly.

“My brother is the biggest primadonna you will ever meet,” Castiel explained. “If you can’t handle him when he’s like this, I would recommend not pursuing a relationship any further.”

It felt kind of like a blessing. A broad smile bloomed over Sam’s face. “Thank you, Castiel, seriously,” he said, and without hesitation, rushed into the coffee shop.

He found Gabriel packing a box marked DONATIONS on one side with more force than the delicate pastries deserved, his back to the door. Sam hesitated. The straight line of his back was somehow forbidding.

He cleared his throat when Gabriel didn’t look like he was going to turn around any time soon. “Not now, Cas,” Gabriel snapped. “I’m thinking.”

“About what?” Sam asked.

Gabriel jumped near out of his skin. He turned slowly around. “How did you get in here?”

“Castiel let me in,” Sam admitted.

“I’m going to wring his scrawny neck,” Gabriel said, edging around the prep station so that it was between him and Sam.

Sam stepped into the room, shoving his hands in his pockets to hide his nerves. “Did you read my card?”

Gabriel’s lips flattened into an unhappy line and his eyes flickered to the side. “Yes, I got your card, Sam.”

The lingering hope fizzled. “So that’s a no,” Sam said.

Gabriel smacked both his hands on the prep station. His eyes were wide and hurt, like Sam was twisting in a knife. “Stop—toying with me,” he pleaded. “I know I'm just a—a weird coffee shop owner, and you don't even know me and never asked for this stupid crush, and—and I didn’t even know you were a lawyer.” He folded in on himself, hands braced on the prep station, and laughed slightly, like he couldn’t believe how ridiculous he was being—which was saying something since Gabriel seemed like he could be a pretty ridiculous guy. “But—I really liked you, Sam, and I’d really like to get over you now.”

Sam’s breath strangled in his throat and he strode forward to grab Gabriel’s shoulders. It almost felt like something between them was dying, and Sam was _not_ about to let that happen.

“You're right. You are kind of weird, and you can be kind of a dick.” He grimaced. “Not that that’s a bad thing, since so can I, clearly. And I _don’t_ know you, but I’d really like to _get_ to know you.” Sam swept a lock of hair of Gabriel’s face, gently tilting his face up with both of his hands. “The card wasn’t some sort of malicious prank. I meant what I said. I want to start over. Prove to you that I’m more than just some sort of oblivious dumbass.”

“Sam—”

“Please, Gabriel. Just—give it a chance?”

Gabriel stared up at him. His eyebrows were crumpled together, still wounded. They stood in silence for several heartbeats, and then Sam stepped back, drawing his fingers away from Gabriel’s face. Before he could pull completely away, Gabriel fell forward, headbutting his chest.

“Fine,” Gabriel grumbled.

Sam gripped Gabriel’s arms. “Seriously?”

“Well, how was I supposed to say no to that?” Gabriel asked, pulling back slightly. His lips twitched when he caught sight of Sam’s expression. “You mook.”

Sam beamed at him, lifting a hand to drag the pad of his thumb across Gabriel’s cheek. “Can I kiss you?”

Gabriel’s lips quirked into that vulpine smile. “I thought we were starting over. You’d kiss someone you just met? Just how easy do you think I am, Winchester?”

“I guess I could wait until the third date,” Sam said, leaning down to rest their foreheads together.

“The correct answer is ‘super easy’,” Gabriel said, then surged up to kiss his way into Sam’s laughing mouth.


	6. Epilogue

The cupid sat in the mostly empty coffee shop. He had dressed in an cheerful red suit covered in little maroon hearts for this wondrous occasion. Although Paradise Found had been closed for over thirty minutes, Sam was leaning against the counter, watching fondly as Gabriel mixed a drink with one hand and waved around his other as he energetically recounted the time he’d successfully convinced his older brother that unicorns were real.

The cupid clutched his chest with both hands even though he, technically, didn’t have a heart. It had been touch and go for awhile there. At one point Gabriel’s mark had almost completely faded, but Sam had pulled through in the end and, once again, true love prevailed. He wiped the corner of one eye and sniffled, overcome with happiness.

Gabriel handed the drink to Sam, who snorted a messy laugh. Curious, the cupid drifted over to the counter to peer into the mug. Gabriel had drawn a rather anatomically correct penis in foam and was looking very smug about it.

“What’s this?” Sam asked, lifting the mug to his nose. His eyes fell shut in appreciation. “It smells amazing.”

“Just a new recipe I wanted to try,” Gabriel said, leaning against the counter next to Sam.

Sam blew on the penis (which made Gabriel huff out a dirty laugh) and sipped the coffee. His eyes drifted shut and he hummed his appreciation. “Gabriel, this is really good.”

Gabriel’s soul glowed with pleasure at the compliment. He shuffled closer to Sam, pressing their shoulders together. “Not too sweet?”

“It’s incredible,” Sam said, taking another long pull from his coffee. “What is it?”

“Blackberry Lavender Latte. I’m thinking about putting it on tomorrow’s menu.”

“You can do that?” Sam asked, lowering the mug.

Gabriel cocked his head to the side. “Of course I can.”

“I mean, don’t you need to run it by your boss or something?”

Gabriel pursed his lips together, eyes glimmering with amusement. “Just who do you think my boss is?”

Sam scratched the back of his head. “Uh, I’m not sure. Some corporate asshole?”

“Sam. I _own_ Paradise Found,” Gabriel laughed. “Dumbass.”

“Wait, seriously?” Sam said, surprised, and then ridiculously thrilled and proud of his boyfriend. The cupid sighed happily. He almost didn’t need to anything at all.

Almost.

He lifted a hand and shot a finger gun at Sam. Sam’s excited expression faded into something sweet and wondering, and he set his mug on the counter. 

“Wait, Sam,” Gabriel cackled when Sam pulled him into his arms. “How could I have gotten away with—” Whatever he was going to say next was cut off when Sam ducked down at kissed him, soft and tender, until all the laughter had faded and Gabriel was trembling in his arms.

“Oh,” Gabriel exhaled when Sam finally pulled back, his eyes wide and slightly glazed. “Wow. Listen, I really don’t want to jeopardize my health score, so if you want to take me back to your place—”

Sam snorted, but caught Gabriel’s hand and tangled their fingers together. “Let’s go.”

The cupid sighed again, face blooming into a dreamy smile. Now, if his next job would work out just as perfectly. He clapped his hands and appeared in front of a brown building accented with red. Students streamed out of Truman High, laughing and jostling each other, or staring down at their cellphones. A teenager with messy blond hair and sad eyes trudged down the stairs by himself, his hands shoved in his pockets and his shoulders slumped.

“Adam, wait.”

Adam turned around, quirking a sardonic smile as Castiel pushed out of the school. “What’s up, Mr. Milton?”

“Listen, I know things are rough for you right now,” Castiel said, earnest and clumsy. He wasn’t really equipped to deal with emotions, but was willing to try. It was why he was such a popular teacher. “I wanted to offer my condolences and let you know you can talk to me. If you need to.” He winced, mostly at himself. “Or want to.”

Adam’s smile became a little more genuine. “Thanks, teach. I’ve got family here. It—helps.”

A sleek black muscle car roared up to the curve and a couple of students stopped to admire the beauty. Adam glanced at the car, shifting his backpack.

“Of course,” Castiel said, nodding seriously. “Family is very important.”

The door to the Impala creaked open and Dean swung out, slamming the door behind him. Castiel’s eyes drifted to him, as if drawn to the sun. The cupid shot his finger gun. Castiel lifted one hand to clutch his chest in shock.

“Mr. Milton?” Adam asked, concerned. Castiel just gaped at Dean.

“Hey, Adam,” Dean called, hopping onto the curb, then slowing when he caught sight of Castiel. The cupid pointed his finger at Dean’s chest and fired. He wasn’t about to make the same mistake twice.

To his credit, Dean didn’t even stumble. His eyes widened slightly, then narrowed into an almost predatory smile. “Well well well, if it isn’t Castiel Milton,” Dean said.

“Ah, shit,” Castiel said, succinctly.

Adam snorted a laugh, drawing their attention back to him. “You two know each other?”

“We’ve met,” Dean said.

“Unfortunately,” Castiel muttered. He shook his head, as if trying to shake off Dean’s presence, and clapped Adam’s shoulder. “I meant what I said. If you need anything, don’t hesitate to ask.

Some of the tension around Adam’s eyes melted away and he smiled crookedly at Castiel. Castiel smiled awkwardly back, stared briefly at Dean, and then, without another word, turned around and ran away.

Dean watched Castiel retreat, and then led Adam to the Impala. The cupid frowned. Maybe it would be best if he kept an eye on Dean and Castiel for the time being. He had a feeling they would need all the help they could get.

**Notes for the Chapter:**

> Sabriel prompts welcome @writeonclara :)


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